1: 62 percent / 1) LiNH2 / 1) liq. NH3 - THF, -40 deg C, 2) THF - HMPT, 40 deg C, 3 h 2: 90 percent / H2 / 5percent Pd/BaSO4 - quinoline / methanol / Ambient temperature View Scheme

in ammonia 6 h;

1: 66 percent / liquid ammonia / 6 h 2: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 3: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 4: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme